Question

Show how you would convert 2-bromocyclohexanol to the following diol. You may use any additional reagents you need.

Short answer

Different steps involved in the conversion process are as given below.

(1) Protection of hydroxyl group by treating 3-bromocyclohexanol withtriisopropylsilyl chloride(TIPSCl) in presence of triethylamine.

(2) Making Grignard reagent by treating the initial product with magnesium and ether.

(3) Reaction of Grignard reagent with a ketone (butan-2-one).

(4) Hydrolysis ( becomes OH).

(5) Removing the protection by reacting with tetrabutylammonium fluoride (Bu₄N⁺F^-). This gives the final product as diol.

Step-by-step solution

Steps involved in conversion of 2-bromocyclohexanol to the given diol

Different steps involved in the conversion process are as given below.

(1) Protection of hydroxyl group by treating 3-bromocyclohexanol withtriisopropylsilyl chloride(TIPSCl) in presence of triethylamine.

(2) Making Grignard reagent by treating the initial product with magnesium and ether.

(3) Reaction of Grignard reagent with a ketone (butan-2-one).

(4) Hydrolysis ( becomes OH).

(5) Removing the protection by reacting with tetrabutylammonium fluoride (Bu₄N⁺F^-). This gives the final product as diol.

Synthesis

conversion of 3-bromocyclohexanol to diol